DE2328605C2 - Verfahren zur Herstellung eines Diastereoisomerengemisches von Zearalanol - Google Patents
Verfahren zur Herstellung eines Diastereoisomerengemisches von ZearalanolInfo
- Publication number
- DE2328605C2 DE2328605C2 DE2328605A DE2328605A DE2328605C2 DE 2328605 C2 DE2328605 C2 DE 2328605C2 DE 2328605 A DE2328605 A DE 2328605A DE 2328605 A DE2328605 A DE 2328605A DE 2328605 C2 DE2328605 C2 DE 2328605C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- zearalanol
- zearalenone
- mixture
- diastereomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- FPQFYIAXQDXNOR-QDKLYSGJSA-N alpha-Zearalenol Chemical compound O=C1O[C@@H](C)CCC[C@H](O)CCC\C=C\C2=CC(O)=CC(O)=C21 FPQFYIAXQDXNOR-QDKLYSGJSA-N 0.000 title claims description 20
- 229960002300 zeranol Drugs 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 12
- 239000000203 mixture Substances 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000002844 melting Methods 0.000 claims description 18
- MBMQEIFVQACCCH-UHFFFAOYSA-N trans-Zearalenon Natural products O=C1OC(C)CCCC(=O)CCCC=CC2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-UHFFFAOYSA-N 0.000 claims description 18
- MBMQEIFVQACCCH-QBODLPLBSA-N zearalenone Chemical compound O=C1O[C@@H](C)CCCC(=O)CCC\C=C\C2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-QBODLPLBSA-N 0.000 claims description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 235000015165 citric acid Nutrition 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- 230000008018 melting Effects 0.000 description 13
- 238000006722 reduction reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FYUNQERIZAJDPT-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;ethanol Chemical compound CCO.OC(=O)C(O)C(O)C(O)=O FYUNQERIZAJDPT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- CAQZTSCRGMRSHX-ODZAUARKSA-N (z)-but-2-enedioic acid;ethanol Chemical compound CCO.OC(=O)\C=C/C(O)=O CAQZTSCRGMRSHX-ODZAUARKSA-N 0.000 description 1
- PPJUFUHHIKYDPG-UHFFFAOYSA-N C(C)(C)(C)O.P(O)(O)(O)=O Chemical compound C(C)(C)(C)O.P(O)(O)(O)=O PPJUFUHHIKYDPG-UHFFFAOYSA-N 0.000 description 1
- MWKMHTLLGQHDQQ-UHFFFAOYSA-N C(C)(C)O.C(=O)(O)C(O)C(O)C(=O)O Chemical compound C(C)(C)O.C(=O)(O)C(O)C(O)C(=O)O MWKMHTLLGQHDQQ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BMWZKJJCLPAELA-UHFFFAOYSA-N butanedioic acid;ethanol Chemical compound CCO.OC(=O)CCC(O)=O BMWZKJJCLPAELA-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ANBZWDBEKOZNHY-UHFFFAOYSA-N ethanol;oxalic acid Chemical compound CCO.OC(=O)C(O)=O ANBZWDBEKOZNHY-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
-
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03F—AMPLIFIERS
- H03F1/00—Details of amplifiers with only discharge tubes, only semiconductor devices or only unspecified devices as amplifying elements
- H03F1/02—Modifications of amplifiers to raise the efficiency, e.g. gliding Class A stages, use of an auxiliary oscillation
-
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03F—AMPLIFIERS
- H03F3/00—Amplifiers with only discharge tubes or only semiconductor devices as amplifying elements
- H03F3/20—Power amplifiers, e.g. Class B amplifiers, Class C amplifiers
- H03F3/24—Power amplifiers, e.g. Class B amplifiers, Class C amplifiers of transmitter output stages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00292449A US3808233A (en) | 1972-09-26 | 1972-09-26 | Zearalenone reduction |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2328605A1 DE2328605A1 (de) | 1974-04-04 |
| DE2328605C2 true DE2328605C2 (de) | 1986-07-10 |
Family
ID=23124719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2328605A Expired DE2328605C2 (de) | 1972-09-26 | 1973-06-05 | Verfahren zur Herstellung eines Diastereoisomerengemisches von Zearalanol |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3808233A (cs) |
| AT (1) | AT330377B (cs) |
| AU (1) | AU475426B2 (cs) |
| BE (1) | BE805261A (cs) |
| CA (1) | CA980785A (cs) |
| CH (1) | CH587839A5 (cs) |
| DE (1) | DE2328605C2 (cs) |
| DK (1) | DK130464B (cs) |
| ES (1) | ES417199A1 (cs) |
| FR (1) | FR2200263B1 (cs) |
| GB (1) | GB1379859A (cs) |
| IL (1) | IL42623A (cs) |
| NL (1) | NL7311613A (cs) |
| PH (1) | PH10914A (cs) |
| SE (1) | SE383745B (cs) |
| ZA (1) | ZA734356B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2563287T3 (es) | 2009-04-09 | 2016-03-14 | Intervet International B.V. | Un proceso de fabricación de zeranol |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3697548A (en) * | 1970-04-02 | 1972-10-10 | Commercial Solvents Corp | Zearalenone reduction |
-
1972
- 1972-09-26 US US00292449A patent/US3808233A/en not_active Expired - Lifetime
-
1973
- 1973-06-05 DE DE2328605A patent/DE2328605C2/de not_active Expired
- 1973-06-06 CA CA173,325A patent/CA980785A/en not_active Expired
- 1973-06-12 AT AT511973A patent/AT330377B/de not_active IP Right Cessation
- 1973-06-26 ZA ZA734356A patent/ZA734356B/xx unknown
- 1973-06-28 IL IL42623A patent/IL42623A/en unknown
- 1973-06-29 AU AU57512/73A patent/AU475426B2/en not_active Expired
- 1973-07-02 GB GB3149073A patent/GB1379859A/en not_active Expired
- 1973-07-05 CH CH978473A patent/CH587839A5/xx not_active IP Right Cessation
- 1973-07-10 ES ES417199A patent/ES417199A1/es not_active Expired
- 1973-07-17 DK DK394573AA patent/DK130464B/da not_active IP Right Cessation
- 1973-07-18 PH PH14833A patent/PH10914A/en unknown
- 1973-08-02 SE SE7310661A patent/SE383745B/xx unknown
- 1973-08-23 NL NL7311613A patent/NL7311613A/xx not_active Application Discontinuation
- 1973-09-25 FR FR7334287A patent/FR2200263B1/fr not_active Expired
- 1973-09-25 BE BE135997A patent/BE805261A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES417199A1 (es) | 1976-06-01 |
| FR2200263B1 (cs) | 1978-11-10 |
| DE2328605A1 (de) | 1974-04-04 |
| DK130464C (cs) | 1975-07-21 |
| GB1379859A (en) | 1975-01-08 |
| AU5751273A (en) | 1975-01-09 |
| IL42623A (en) | 1976-08-31 |
| PH10914A (en) | 1977-10-04 |
| DK130464B (da) | 1975-02-24 |
| NL7311613A (cs) | 1974-03-28 |
| FR2200263A1 (cs) | 1974-04-19 |
| ATA511973A (de) | 1975-09-15 |
| ZA734356B (en) | 1974-06-26 |
| IL42623A0 (en) | 1973-08-29 |
| CH587839A5 (cs) | 1977-05-13 |
| AU475426B2 (en) | 1976-08-19 |
| CA980785A (en) | 1975-12-30 |
| US3808233A (en) | 1974-04-30 |
| AT330377B (de) | 1976-06-25 |
| BE805261A (fr) | 1974-01-16 |
| SE383745B (sv) | 1976-03-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2907869C2 (cs) | ||
| EP0071787B1 (de) | Neue Ruthenium/Kohle-Hydrierkatalysatoren, deren Herstellung und Verwendung zur selektiven Hydrierung von ungesättigten Carbonylverbindungen | |
| DE1115238B (de) | Verfahren zur partiellen Hydrierung von Acetylenverbindungen | |
| DE19546514B9 (de) | Katalysator und dessen Verwendung | |
| DE60125378T2 (de) | Verfahren zur Herstellung von 2-AMINOMETHYL-HALOGEN-PYRIDINEN | |
| DE2923949C2 (de) | Verfahren zur Herstellung von 1,4-Butandiol durch katalytische Hydrierung von 1,4-Butindiol | |
| DE2418499A1 (de) | Verbessertes verfahren zur herstellung von alpha-6-deoxytetracyclinen | |
| DE2328605C2 (de) | Verfahren zur Herstellung eines Diastereoisomerengemisches von Zearalanol | |
| DE2626676A1 (de) | Verfahren zur herstellung von 2-pyrrolidon | |
| EP0825181B1 (de) | Verfahren zur Herstellung von Carbazol | |
| DE60119188T2 (de) | Verfahren zur Herstellung einer Epoxycyclododecan-Verbindung | |
| DE2111606C3 (de) | Verfahren zur Herstellung eines Diasteroisomerengemisches von Zearalanol | |
| DE2841585C3 (de) | Verfahren zur Herstellung von 2.2-Dialkyl-pentan-1.5-diaminen | |
| DE2626675A1 (de) | Verfahren zur herstellung von 2-pyrrolidon | |
| DE2416584A1 (de) | Hexamethyltetracosan-diol derivate und verfahren zu deren herstellung | |
| DE3028384A1 (de) | Verfahren zur herstellung von n-alkylpiperidinen und n-alkylpyrrolidinen | |
| DE1276032B (de) | Verfahren zur Herstellung von Cyclohexylamin | |
| DE4210311A1 (de) | Verfahren zur Herstellung von Aminen aus Azinen | |
| DE2111618A1 (de) | Verfahren zur Herstellung eines Diastereoisomerengemisches von Zearalanol | |
| DE1668950C3 (de) | Sulfonamidsubstituierte Benzylaniline Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE1768071A1 (de) | Verfahren zur Herstellung von gamma-Hydroxybutyronitril | |
| DE1253715B (de) | Verfahren zur Reinigung von Lactamen | |
| DE1468779A1 (de) | Verfahren zur Herstellung von Dicyclohexylaminen aus Dicyclohexanolen | |
| DE963519C (de) | Verfahren zur Herstellung von N, N'-Dibenzyl-aethylendiamin | |
| DE1179928B (de) | Verfahren zur Herstellung von Carbonsaeure-vinylestern |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |